A likely intermediate during the CO2-induced activation of 2-alkylindoles toward electrophilic substitution: Structure of a unique tetramer formed by joining two boat-shaped (LiOCO)(2) rings | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

7440954

Reference Type

Journal Article

Title

A likely intermediate during the CO2-induced activation of 2-alkylindoles toward electrophilic substitution: Structure of a unique tetramer formed by joining two boat-shaped (LiOCO)(2) rings

Author(s)

Davies, RP; Raithby, PR; Snaith, R

Year

1996

Is Peer Reviewed?

Journal

Organometallics
ISSN: 0276-7333
EISSN: 1520-6041

Publisher

American Chemical Society

Volume

Issue

Page Numbers

4355-4356

Language

English

DOI

10.1021/om960739a

Web of Science Id

WOS:A1996VM85200007

Abstract

Reaction of 2,3-dimethylindole in thf with nBuLi and CO2 gives a lithium carbamate complex (2Â·thf)n, which has a unique tetrameric solid-state structure (n = 4) containing two boat-shaped (-LiO-COLiOCO-) rings joined by four inter-ring Li-O connections. The two-coordinate O atoms of these rings are near to the 2-Me groups of the indolyl residues, suggesting an explanation for second lithiation (and subsequent electrophilic substitution) of 2-alkylindoles and related heterocyclics occurring specifically at the 2-alkyl position.